I am going to combine the last three woes. Jesus intensifies His condemnation of the Pharisees as He continues to levy those accusations against them.
He reiterates that the Pharisees' hypocrisy is too egregious to ignore:
“Woe to you, teachers of the law and Pharisees, you hypocrites! You are like whitewashed tombs, which look beautiful on the outside but on the inside are full of the bones of the dead and everything unclean. In the same way, on the outside you appear to people as righteous but on the inside you are full of hypocrisy and wickedness." (Matt. 23:27-28).
Whitewashing a tomb seems innocent enough, when you are trying to make it look nice for a burial. In fact, when the mourners approach, you don't them to be distracted by a tomb that is not ceremonially prepared and unacceptable. You honor the funeral procession and the dead by presenting a tomb that is really as it appears: ritually clean and ready.
But whitewashing a tomb when there are bones still in it and it is utterly unclean because of that, is another matter entirely. That's a sickening kind of fraud. It appears one way but is really another. And that is not due to error. The person who presents such a tomb totally knows what it wrong, but hopes everyone will ignore it.
Jesus will not and cannot ignore this. The Pharisees are deliberate in their hypocrisy; He is not going to let them pass off their "respectability" without a challenge.
Because that's what prophets do. The Old Testament tradition of the prophet is one who warns, cajoles and laments over what the people are doing and not doing, and how it is an offense to God Himself. Jesus takes on the mantle of a prophet in His denunciations. In fact, the next woe mentions the prophets and how the people (like the Pharisees) responded to them:“Woe to you, teachers of the law and Pharisees, you hypocrites! You build tombs for the prophets and decorate the graves of the righteous. And you say, ‘If we had lived in the days of our ancestors, we would not have taken part with them in shedding the blood of the prophets.’ So you testify against yourselves that you are the descendants of those who murdered the prophets. Go ahead, then, and complete what your ancestors started!"(Matt. 23:29-32).
“You snakes! You brood of vipers! How will you escape being condemned to hell? Therefore I am sending you prophets and sages and teachers. Some of them you will kill and crucify; others you will flog in your synagogues and pursue from town to town. And so upon you will come all the righteous blood that has been shed on earth, from the blood of righteous Abel to the blood of Zechariah son of Berekiah, whom you murdered between the temple and the altar. Truly I tell you, all this will come on this generation." (Matt. 23:33-36).